N-substituted derivative of sulphoanilines



amine, propylamine, butylamine, isobuty'lamine,

and cyclohexylamine, to act upon Patented May 28, 1935 N-SUBSTITUTED DERIVATIVE F SULPHOANILINES Wilhelm Neelmeier and Wilhelm Meiser, Lever- ,kusen-I. G.-Werk, Germany, assignors to General .Aniline .Works, Inc., New York, N. Y., a corporation of Delaware No:-Drawing.' Application September 21, 1933, Serial No.1 690,497. Iii-Germany September 29,

The present invention relates to new derivatives of aniline, more particularly it relates to compounds of the probable general formula:

i z wherein R stands, for alkyll kvl r hydroaryl,

such as methyl, ethyl, propyl; benzyl and cyclehexyl, one 1: stands fora sulphonic acid group .g and the other 3: stands for azsulphonic or for a carboxylic acid group;

In accordance with the present invention these products are prepared by causing a primary amine of the aliphatic, araliphatic or hydroaromatic series, such as methylamine, ethylbenzylamine a halogenbenzene of the ,probable general formula:

255;, halogen wherein one a: stands for a sulphonic acid group and the other a: stands for a sulphonic or carboxylic acid group, in an aqueous medium and at elevated temperature.

The temperatures used may be varied between the widest limits. As a general rule, however, there may be stated that the process may be carried out at temperatures between about 50 and about 200 C'.; advantageously the process is carried out at temperatures between about 100 and 150 C. with the addition of copper or a copper compound as catalyst and with excess alkyl-, aralkylor hydroaryl-amine.

Our new compounds are generally colorless substances, forming easily water soluble alkali metal salts; they are valuable intermediate products in the manufacture of dyestuffs and synthetic drugs.

The invention is illustrated by the following examples, without being limited thereto, the parts.

being by weight: v

Example 1.-316.5 parts of the neutral sodium salt of chlorobenzene-2.4-disulphonic acid are heated in an autoclave for 20 hours at 130 C. with 5 Claims. (01. 260-109) 100 parts of water, 500 parts of an aqueous monomethylamine solution of 50% strength, 1 part of copper powder and 1.5 parts of cuprous chloride. After cooling, the reaction mixture is rendered alkalinev to caustic soda, and the excess methyla-mine is distilled off with steam. From the remainder the copper 'is filtered, and the V filtrate contains the methylaniline-2.4-disulphonic. acid of the, formula:

, NH-CHa in ayield of of theory. T i 11 l Example 2.-238 partsof the neutral sodium salt of chlorobenze-ne-4-sulpho-2-carboxylic acid (of a content of 85%;);arerefluxed for 10 hours with stirring with 80 parts of water, 240 parts of n-butylamine, one part of copper powder and 0.5 part of cuprous chloride. The working up is performed as described in Example 1. The nbutylaniline--sulpho-2-carboxylic acid of. the formula? NHCH2-CH1-CH -CH3 GOOH . similar properties.

Example 3.-118 parts of chlorobenzene-Z-sulphol-carboxylic acid are dissolved with parts of water and 120 parts of aqueous caustic soda lye of 33% strength to a neutrally reacting solution. Thereto are added 300 parts of isobutylamine, and the mixture is heated in an autoclave for 20 hours CH3 ITIH-CHz-CE CH; S OaH 1 C O OH is precipitated in form of a colorless powder by the addition of formic acid.

We claim:

1. Compounds of the general formula:

x wherein R stands for alkyl, a radical of the cyclo- 'hexyl or benzyl series, one x stands for a sulphonic acid group and the other :1: stands for a sulphonic or for a carboxylic acid group, being generally colorless substances, forming easily water soluble alkali metal salts and being valuaable intermediate products in the manufacture of dyestuffs and synthetic drugs. I 7

2. Compounds of the general formula:

COOH

S 03H wherein R stands for alkyl, a radical of the cyclohexyl or benzyl series, being generally colorless substances, forming easily watersoluble alkali metal salts and being valuable intermediate products in the manufacture of dyestuffs and synthetic drugs.

3. Compounds of the general formula:

COOH

03H wherein alk stands for alkyl of 1 to 5 carbon atoms, being generally colorless substances, forming easily watersoluble alkali metal salts and being valuable intermediate products in the manufacture of dyestufis and synthetic drugs.

4. The compound of the following formula:

lTIH-CHa COOH SI 03H being a colorless substance, forming easily watersoluble alkali metal salts and being a valuable intermediate product in the manufacture of dyestufis and synthetic drugs. 5. The compound of the following formula:

OOOH

I S 03H soluble alkali metal salts and being a valuable intermediate product in the manufacture of dyestufis and synthetic drugs. WILHELM NEELMEIER. WILHELM MEISER.

being a colorless substance, forming easily water- 

